7 Timeless Pencil-Skirt Outfits for Any Age

Pencil skirts are without a doubt a closet staple that every woman should own. This silhouette is one that surpasses time and trend, and we are here to prove it to you with the timeless pencil-skirt outfits ahead. Thanks to their simplistic lines and typically conservative length, pencil skirts are not confined to a certain age group nor personal style, either.

Celebrities like Kendall Jenner and Reese Witherspoon demonstrate how to style this timeless skirt in a way that fits your own personal style. Whether the addition of a simple button-down for work is what you're looking for, or the combination of a newsboy cap and velvet ankle boots is more your vibe, fear not, because the pencil-skirt outfits ahead will satisfy a spectrum of tastes and ages.

Keep reading to see the pencil-skirt outfits you should be trying and to shop some of our favorites.

Jennifer Lopez


(Image credit: Splash News)

What You'll Need: A thin white knit, nude heels, and simple jewelry.

Kendall Jenner


(Image credit: Splash News)

What You'll Need: A newsboy cap, a choker, a white tee, and velvet boots.

Lauren Hutton


(Image credit: Style du Monde)

What You'll Need: A cable-knit sweater, a gray tee, and sneakers.

Jessica Alba


(Image credit: Splash News)

What You'll Need: Hoop earrings, a black tank, and black pumps. 

Sarah Rutson


(Image credit: Style du Monde)

What You'll Need: A structured poplin top, sneakers, and timeless shades.

Reese Witherspoon


(Image credit: Splash News)

What You'll Need: A classic button-down, printed loafers, and a polished bag.

Amal Clooney


(Image credit: Splash News)

What You'll Need: A fitted tee, pumps, and a statement bag. 

Shop pencil skirts we love:

Lauren Eggertsen
Editorial Director

"Copy (200 words): Lauren Eggertsen is currently the editorial director of Who What Where and has worked at the company for nearly seven years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Sydney Sweeney, Lindsay Lohan, and Megan Fox. 

She has also attended multiple fashion weeks, including New York, London, and Milan, where her personal style has been featured on sites such as Elle.com, HarpersBazaar.com, and Vogue.co.uk. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.